Chloroacetonitrile → (4-Formyl-3,5-dimethyl-phenoxy)-acetonitrile

HRID 1514884Notes

Reaction equation

HRID 1514884 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.Cl[CH2:13][C:14]#[N:15].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH:6]([C:5]1[C:4]([CH3:11])=[CH:3][C:2]([O:1][CH2:13][C:14]#[N:15])=[CH:9][C:8]=1[CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 86651260(4-Formyl-3,5-dimethyl-phenoxy)-acetonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxy-2,6-dimethyl-benzaldehyde (150 mg), chloroacetonitrile (0.1 mL), and Cs2CO3 (390 mg) in acetone (10 mL) was stirred at room temperature for 16 h. The mixture was concentrated, diluted with water, and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification by column chromatography (SiO2, 3:1 hexane/EtOAc) gave (4-formyl-3,5-dimethyl-phenoxy)-acetonitrile.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 3:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-d05e4297aa99421583d029300f3f0d0a
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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